Josh Winigrad

Josh Winigrad is an accomplished professional with extensive experience in business operations and consulting. As the founder of Self Bill Pro since June 2023, Josh Winigrad drives innovation in workforce management solutions. Previously, as Managing Director at Beneration from December 2016 to May 2023, Josh Winigrad led diverse teams across finance, recruiting, and service delivery, while developing cost-saving strategies for employers in the insurance sector. In an earlier role as Entrepreneur In Residence at Archetype, Josh Winigrad supported company growth through innovative consulting and venture models. Additionally, as Operations Transformation Analyst at Sungard Availability Services, Josh Winigrad focused on enhancing global operational performance through data analysis and solution implementation. Josh Winigrad began a career in manufacturing as a Manufacturing Process Engineer at Aluminum Shapes LLC, where Lean/Six Sigma methodologies were applied to optimize production processes. Educationally, Josh Winigrad holds a Bachelor of Science in Business Administration, specializing in Operations and Supply Chain Management from Drexel University.

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Philadelphia, United States

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Self Bill Pro

There aren’t many industries that take payment on an honor system, one where you literally get to bill yourself. At Self Bill Pro, we’re helping take the self-checkout lane out of grocery stores and into employee benefits. Our goal is simply to provide HR departments with accurate, comprehensive, and timely self-bills, making sure they don’t lift one finger in the process.


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